With less than 100 days until the election, we have now officially entered the unforgiving phase of the presidential election cycle. In a traditional election, the mistakes that Donald Trump made this past week, such as attacking the family of a fallen soldier, or not endorsing senior members of one's party, or not understanding whether or not Russia invaded Ukraine, would have proven disastrous. But this is no traditional election – or is it? While it's easy to believe that in this "bizarro" election Trump can survive this week, there are some brutal realities that the GOP candidate can no longer avoid facing.

How many more days can he lose? Good campaigns ask themselves: Are they winning the day? This is not about polls, per se. Rather, this is about whether a campaign is getting its message out effectively and clearly. Is it winning over more voters than it is losing? Or, is the campaign on the defensive because of some ill-thought out or ill-tempered remark? Based on these criteria, Trump has had about as bad of a set of days as any candidate in recent presidential election history. Now, if this were January 2016, maybe he could recover, but at this stage in the election, Trump's biggest enemy is not just himself – it is time. Every day lost dealing with a series of self-inflicted wounds is a day that can't be recovered. With national polls now showing him trailing Hillary Clinton by as many as 10 points-and with the Olympics and Labor Day break coming up to grab voters' attention-he is running out of time. Which leads to one conclusion that every losing campaign eventually faces: go even more negative.

How much will the battleground map shrink? Traditionally, if you want to know where each candidate stands, all you have to do is look at their schedule or where their ads are playing (or not playing). Even in this chaotic race, it will likely come down to eight key states (NV, FL, OH, IA, NC, VA, PA, NH). While it is still relatively early, and early polling is sporadic, the challenge for Trump is that the map is expanding to Clinton's advantage with states such as Arizona and Georgia now becoming possible battlegrounds. In contrast, while Trump still has a path to 270 – his map is not expanding, but is instead, arguably, shrinking. States that Trump has trumpeted as potential battlegrounds, like New York or California, have not materialized. Given that national polls often lead state polls, the next batch of battleground polls in key states of Ohio and Pennsylvania could prove to be threatening to Trump's electoral hopes.

How prepared will he be for the first debate: The first presidential debate between Trump and Clinton will have HUGE ratings. It will be blown up by the media into some Herculean struggle for the fate of the nation – and would that be wrong? For Trump, if his downward slide continues and Clinton does not make an unforced error, the first debate will be the moment that will either help resurrect his campaign or completely finish it off. The stakes will be that high for Trump. In a traditional campaign, weeks of debate prep and policy briefing will help get the candidate ready. The problem for Trump is that preparation requires staff, expert advisors, and time – all of which he has very little of. If Trump actually prepares with facts and substance he could, in theory, hold his own against Clinton, but that's not Trump's style, is it? Who will prepare him to debate the vagaries of foreign and domestic policy is not a rudimentary question. It will help decide whether the American people see Trump as ready to be president, because right now they don't, and he is only feeding into that perception further with his erratic and uninformed policy statements.